Shug McGaughey seeking first Kentucky Derby win

He stops. He talks. He tells stories, pouring his Kentucky drawl over the conversation like syrup.

He makes jokes. He has time for everyone. He opens up, a closed fist slowly unclenching.

"I have not been like this in a long time," Shug admitted. "Maybe ever, really. … I've enjoyed doing this as much as I have in a long, long time."

Imagine that. Enjoyment and the Kentucky Derby, forever mutually exclusive for Claude R. McGaughey III, are having a karmic convergence this spring.

Following Wednesday's post draw for the 139th Derby, the 62-year-old trainer now has the favorite in Orb – winner of his last four races, including the Florida Derby. The 3-year-old was installed as the early 7-2 favorite after drawing the No. 16 post. The handsome son of Malibu Moon has trained sensationally at Churchill Downs, becoming the buzz horse of Derby Week.

If so, it's about time. Which leads us back to the Hall of Famer's noticeable shift toward contentment.

For most of his career, Shug has been a little ball of stress leading up to the biggest races. He was rarely discourteous, but rarely welcoming, either. He was not curt, but never expansive. Visitors to his barn were tolerated, but not enjoyed.

Shug took his business very seriously, and that was abundantly clear to all who encountered him. You could almost see the burden of internal expectation weighing on his shoulders.

"At one time I thought I had to win every race," he said. "The more you learn about it, the more you know you can't win every one."

Over time, Shug has won almost every major American race. His 10 Breeders Cup victories are second-most among all trainers. He's won every major stake in his primary racing state of New York, including the Travers and Jockey Club Gold Cup three times apiece.

But the Triple Crown races have been another matter. Part of that is the fact that McGaughey's blueblood owners, Stuart Janney III and Dinny Phipps, are as old-school as it gets – they won't rush a 3-year-old into the spring classics for any amount of money or prestige, since the kingpins of Bessemer Trust and Brahmin of racing already have both in bulk. Part of it is the fact that Shug has readily gone along with that game plan, refusing to jeopardize the development of young horses in pursuit of Triple Crown glory.

And the third part of it is that the rare forays into the Derby, Preakness and Belmont have so often been met with disappointment. Shug has won hundreds of big races, but just one Triple Crown race – the 1989 Belmont with Easy Goer. The rest of the record is riddled with frustration.

And the most frustrating of all has been the race nearest to Shug's heart: The Kentucky Derby.

"I think it's a lifelong dream," said Coleman Connell, a golfing buddy of Shug's who owns a cotton plantation in Clarksdale, Miss. "It's been a while, as you know. Growing up in Kentucky, to come back there and win that race, I know it would mean the world to him."

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He's had six previous entries in America's greatest race, no winners. Easy Goer, son of Secretariat, arrived with towering hype in 1989 but was upset by Sunday Silence while running a dull second. Regally bred Saarland was the second betting choice in 2002 but finished a dawdling 10th.

In between those two was the frustration of Coronado's Quest, in 1998. That colt won the Wood Memorial and might have been the Derby favorite but was basically benched by Shug before the race for bad behavior – he acted up repeatedly. After surgery to fix an entrapped epiglottis that hindered his breathing, a calmer Coronado's Quest reaffirmed his quality later that year by winning the Haskell Invitational and Travers.

Those were great victories. But for a native of Lexington, Ky., not the greatest.

"There's other races," he said. "But there's none that means more to me than this one."

He attended his first Derby as a teenager, catching a spare ticket and a ride to Louisville from a neighbor in 1967. He watched Damascus win that year. The horse was trained by Frank Whiteley, who Shug would ultimately work for one day.

A seed was sewn. Shug went to work as a groom – raking stalls and tending to the mundane needs of thoroughbreds – and eventually dropped out of Ole Miss to continue his work at the track. By 28 he struck out on his own as a trainer, and after solid early success on the New York racing circuit he was named the private trainer of Phipps Stables at 35.

This was like being named the manager of the Yankees at an early age. The black silks and the cherry-red ball atop the jockey's helmet were akin to pinstripes in the racing world.

But to whom much is given, much is expected. And Shug expected the world of himself. In a sport where the best trainers rarely win more than 30 percent of their races, he beat himself up for not batting 1.000.

"I would walk out of [the race track] and feel like I was embarrassed," Shug said. "That I had failed. That I hadn't done what I needed to do.

"I blamed myself. But I'm not sure I didn't blame others, too. There probably was some yelling and screaming."

By 1988, Shug had browbeat himself and his barn into top contention. At age 37, Shug had the best hand in America: Personal Ensign was an undefeated filly; Seeking the Gold was a Travers winner; Easy Goer was a 2-year-old star in the making; Mining was a star sprinter.

He took that armada to Churchill Downs for the Breeders Cup with expectations of four smashing victories – something nobody has done in a single Cup, before or since. On a cold, misty, miserable day, Shug was handed a mixed bag: Personal Ensign rallied for an epic victory to finish her career undefeated; but Easy Goer and Seeking the Gold both finished second and Mining was a disappointing also-ran.

After the Classic was run in darkness, Shug shambled dejectedly back to his barn when a voice asked him how his day went.

"One win, two seconds and a no-good," Shug answered.

"Well," the man said, "you had a good day."

That's when Shug peered more closely at the voice in the darkness and saw it belonged to Charlie Whittingham, the Bald Eagle, one of the greatest trainers in racing history. This was the literal voice of perspective, imparting an undeniable truth: you can't win them all, and you'll go crazy if you can't accept that.

"I've thought back a lot of times on that," Shug said. "That was a huge learning curve for me. With the experience under my belt, the confidence level is a lot higher. I know what to expect."

He expects to win Saturday, but Shug told himself one other thing before this Derby: "We're going to have fun." And so far, he has.

McGaughey has spent more than five weeks in his old Kentucky home, his longest stay in decades. He was in Lexington for most of April, racing at the beautiful boutique track, Keeneland. Last week he moved his operation to Churchill and hunkered down at a nearby Hilton Garden Inn.

Since then, Shug has contentedly spent more than 12 hours a day at the track with his horses, then grabbed Mexican food or stopped at the Cardinal Hall of Fame Café for dinner. At night he watches sports – the NFL draft last week, and the Final Four earlier in April.

"I'm a UK fan and I do not pull for Louisville," Shug said. "But I was glad for Rick [Pitino]. I like Rick. He's a great coach."

Pitino is part-owner of Goldencents, one of 19 challengers to Orb. Shug's colt may well go to the post as the favorite in the Derby, but that guarantees nothing. Field size, distance and competition make this the hardest race in the world to win.

Shug McGaughey, native son, is all too familiar with the difficulty. And the longing it can create.

"I don't really know that I need [a Derby win] to punctuate my career," he said. "But I need it myself. It is something I terribly do want.

"I just can't imagine what it would be like to wake up on Sunday morning and know you won the Kentucky Derby."

In one way, Shug McGaughey already has won. For the first time, he has enjoyed and appreciated the journey to reach the Run for the Roses.